Ben Quilty is sitting opposite his painting, Evening Shadows. It's a sweeping landscape that uses the Rorschach test to produce the inkblot effect, two halves of an image mirror one another.
While he considers this painting, one of many in the career retrospective of Quilty's work now showing at the Art Gallery of NSW, Quilty the artist appears to exist in a Rorschach test of his own making.
On one half there is the man in the gallery today: winner of both the Archibald and Doug Moran Portrait Prize. Celebrated artist, accidental activist. Father.
And on the other half is the boy he once was. Reckless, talented, angry.
Back in 1991 that boy was sitting in this same spot.
As a high school student, Quilty's major work was accepted into ARTEXPRESS, marking the first time he would exhibit at the Art Gallery of NSW.
"It's mind-blowing really," says Quilty on his full-circle moment.
"The work that got into ARTEXPRESS was made the night before it was due. I was out of control as a teenager, dealing with violence, at 17-years-old, I was off the rails."
The hangover of Quilty's tough upbringing has always been apparent in his work. His earliest paintings, hurried portraits of a much-loved Holden Torana speak to a boy searching for meaning, anywhere he could find it.
"That car was everything to me," he says.
"My friends and I would talk shit, get blind, smoke bongs, take drugs and fix the car."
For Quilty, it was a form of initiation. "That was me learning how to become a man."
A single Torana painting hangs near the entrance to the Quilty retrospective (opposite his Archibald-winning portrait of Margaret Olley), a nod to his past.
The treacherous making of a man is a theme that Quilty can't seem to stay away from. Long before 'toxic masculinity' filled column inches, the artist was exploring it on the canvas.
"I've been talking about it for twenty years, trying to understand men, and myself," he says.
"The toxicity of masculinity comes out of the fact that we don't let boys become men in the right way; we just expect it."
Quilty points to his misspent youth – fixing cars, breaking the law, feeling low, getting high – as proof that without guidance, young men are dangerously malleable.
"We end up with boys looking for a rite of passage to prove their manliness, so they start taking drugs or fighting."
"My close Indigenous friends have told me about the long ceremonies their young men go through on the way to adulthood, but what do we have?"
"You get drunk on your 18th birthday, then wake up the next morning, and you're a man? That doesn't work."
Perhaps Quilty's current fixation with the search for modern masculinity comes from his home life.
Together with wife, Kylie, Quilty has two children, Olivia,10, and Joe, 13.
Both are on the brink of shedding their childhood skins and embracing all the confusing baggage that comes with growing up. But with Joe particularly, Quilty seems determined to be the male model he once craved.
"I'm very open and honest with him, he'll never be able to say I kept anything from him, I celebrate every milestone, and I always tell him how well he's done," says Quilty.
"I also tell his mates how well they're doing, and I do it in front of the other boys, and you can see the surprise in their faces."
"They are looking for anyone who is going to celebrate their masculinity, support them and challenge them in a safe environment."
The very nature of a career retrospective forces both the subject and the audience to reflect on what has come before.
Hanging throughout Quilty are reminders of the places the artist has been and the things he's seen.
Portraits from his time as the official Australian War Artist in Afghanistan, artworks documenting the trips to Syria, the cursed plight of refugees.
Then comes the most arresting and recognisable moment of the Quilty back catalogue, the face of Myuran Sukumaran.
A convicted drug smuggler and member of the Bali Nine, Myuran and Quilty developed a famous friendship inside the walls of Kerobokan prison.
They remained close up until Sukumaran's death by firing squad on 29th April 2015. In the days that followed Quilty emptied his grief onto the canvas.
"I really like that painting," says Quilty, pointing to the portrait of his slain friend.
"It was completed a day or two after he was shot, the further I get away from that time the more I realise what an amazing privilege it was to be in his life."
"Myuran faced his mortality like no one else I've ever witnessed, he became a compassionate role model, a man who realised his mistakes, made amends and then faced down death."
Quilty admits that mortality is something he thinks about "more often than not, these days." Maybe it's the trade-off for a life well-lived, maybe it's just middle age?
"It is the one thing none of us knows how to handle," says Quilty, who turns 46 later this year.
"I heard someone say the other day life is not a practice run; I quite like that."
As we finish up, I asked Quilty which he is most proud of, gesturing to the work around us.
"Last weekend I played third-grade cricket with my son, I opened the batting and Joe came in at number five," says Quilty, wonderfully missing the point.
"Full-grown men were sending down steamers, but he held his own, and it was one of the great moments of my life, to bat with my son. I was almost in tears through my helmet."
Quilty, Art Gallery of NSW, November 9, 2019 until February 2, 2020.